86633-20-7Relevant academic research and scientific papers
A Catalytic Cross-Olefination of Diazo Compounds with Sulfoxonium Ylides
Neuhaus, James D.,Bauer, Adriano,Pinto, Alexandre,Maulide, Nuno
, p. 16215 - 16218 (2018/11/23)
A ruthenium-catalysed cross-olefination of diazo compounds and sulfoxonium ylides is presented. Our reaction design exploits the intrinsic difference in reactivity of diazo compounds and sulfoxonium ylides as both carbene precursors and nucleophiles, which results in a highly selective reaction.
A Tunable Route to Prepare α,β-Unsaturated Esters and α,β-Unsaturated-γ-Keto Esters through Copper-Catalyzed Coupling of Alkenyl Boronic Acids with Phosphorus Ylides
Bi, Hong-Yan,Liu, Feng-Ping,Liang, Cui,Su, Gui-Fa,Mo, Dong-Liang
, p. 1510 - 1516 (2018/03/05)
A tunable strategy to prepare α,β-unsaturated esters and α,β-unsaturated-γ-keto esters in good to excellent yields was developed through copper-catalyzed oxidative coupling of phosphorus ylides with alkenyl boronic acids under mild conditions. The reaction without water afforded α,β-unsaturated esters, ketones, and amides while α,β-unsaturated-γ-keto esters, 1,4-α,β-unsaturated diketones and α,β-unsaturated-γ-keto amides were obtained when using 5.0 equiv. of water. H2O18 labeling experiments showed that water played an important role in the formation of α,β-unsaturated-γ-keto esters. A plausible formation mechanism for α,β-unsaturated esters and α,β-unsaturated-γ-keto esters was proposed based on mechanistic studies. Phosphonium salts could also be used directly as coupling partners instead of phosphorus ylides. The reaction exhibited a broad substrate scope, good functional group tolerance, good regioselectivity, and diverse coupling products. (Figure presented.).
A robust multifunctional ligand-controlled palladium-catalyzed carbonylation reaction in water
Gao, Pei-Sen,Zhang, Kan,Yang, Ming-Ming,Xu, Shan,Sun, Hua-Ming,Zhang, Jin-Lei,Gao, Zi-Wei,Zhang, Wei-Qiang,Xu, Li-Wen
supporting information, p. 5074 - 5077 (2018/05/26)
A novel, hydrophilic and recyclable methoxypolyethylene glycol (PEG)-modulated s-triazine-based multifunctional Schiff base/N,P-ligand L9 was prepared and used in Pd-catalyzed Heck-type carbonylative coupling reactions, affording diverse chalcone derivatives and 1,4-dicarbonyl esters in good yields.
Isothiourea-mediated one-pot synthesis of functionalized pyridines
Stark, Daniel G.,Morrill, Louis C.,Yeh, Pei-Pei,Slawin, Alexandra M. Z.,O'Riordan, Timothy J. C.,Smith, Andrew D.
, p. 11642 - 11646 (2013/11/06)
Acids to bases: The synthesis of 2,4,6-trisubstituted pyridines from (phenylthio)acetic acid and a range of α,β-unsaturated ketimines is reported. This process proceeds by intermolecular Michael addition/ lactamization, thiophenol elimination, and N- to O
Synthesis of 3-benzoyl acrylates/acrylamides via Dehydrogenation of 3-benzoyl propionates/propionamides using IBX/p-TsOH
Li, Ziyuan,Wang, Yiyun,Tang, Changhua,Xu, Jinyi,Wu, Xiaoming,Yao, Hequan
experimental part, p. 1301 - 1305 (2010/11/19)
Dehydrogenation by IBX/p-TsOH is applied to the conversion of 3-benzoyl propionates/propionamides to 3-benzoyl acrylates/acrylamides in moderate to excellent yields. The reaction time for the dehydrogenation of 3-benzoyl propionamides was remarkably short
Highly enantioselective organocatalytic Michael addition of nitroalkanes to 4-oxo-enoates
Lu, Hai-Hua,Wang, Xu-Fan,Yao, Chang-Jiang,Zhang, Jian-Ming,Wu, Hong,Xiao, Wen-Jing
, p. 4251 - 4253 (2011/03/19)
A useful Michael addition reaction using nitroalkanes as the nucleophile and 4-oxo-enoates as the Michael acceptor has been disclosed, and the reaction allows expedient access to functionalized chiral γ-keto esters in high yields and excellent enantioselectivities (up to 98% ee), with a low catalyst loading.
Synthetic Utility of the Palladium-Catalyzed Coupling Reaction of Acid Chlorides with Organotins
Labadie, Jeff W.,Tueting, David,Stille, J. K.
, p. 4634 - 4642 (2007/10/02)
The palladium coupling of acid chlorides with unsymmetrical organotin reagents R''3SnR' can be carried out in chloroform under mild conditions in high yields to give the ketone RCOR'in which only one of the four organic groups on tin appears in the ketone product.Alkyl partners (R''= methyl or butyl) on tin serve as anchoring groups and do not transfer.When R' is acetylenic, vinyl, aryl, methoxymethylene, allyl, or benzyl, transmetalation takes place preferentially, resulting in coupling with the acyl group from the acid chloride.The reaction is tolerant of functional groups both on the acid chloride and the tin reagent.A palladium-catalyzed coupling reaction of an organotin reagent bearing acrylate functionality with an acid chloride serves as a method to introduce both a ketone and an acrylate functionality into a carbon framework.The coupling reaction of 4-(tert-butyldiphenylsiloxy)pentanoyl chloride with benzyl 3-(tributylstannyl)acrylate gave a 71percent yield of benzyl 7-(tert-butyldiphenylsiloxy)-4-oxo-2-octenoate, a precursor to the macrolide antibiotic pyrenophorin.
